Quinolin compounds and process of producing same.



PATENT orifice. 1

ALEX B. DAVIS, OF INDIANAPOLIS, INDIANA, ASSIGNOR TO THE ELI AND COMPANY, OF INDIANAPOLIS, INDIANA, A CORPORATION OF INDIANA.

No Drawing.

and useful Improvements in Quinolin Com pounds and Process of Producing Same, of which the following is a specification.

The invention relates to new compounds of the quinolin series prepared by boiling together in solution equimolecular proportions of pyruvic acid, an aldehyde, and an ester of para-amino-benzoic acid. The new compounds. are all derivatives )f 2-phenylquinolin 4:6 dicarboxylic acid. These derivatives are valuable pharmaceutical compounds.

Compounds prepared in this way are: 2- meta para dioxymethylene phenyl quinolin -1z6 dicarboxylic acid-6-ethyl-ester, (from heliotropin, para-amino -ethyl -.benzoate, and pyruvic acid) 2-phenyl-quinolin 4: 6 dicarboxylic acid 6 ethyl ester, (from benzaldehyde, para-amino-ethyLbenzoate, and pyruvic acid). '2- orthooxyphenyl i quinolin 4: 6 dicarboxylic acid 6- ethyl-e'ster, (from salicylic'aldehyde, paraamino-ethyl benzoate and pyruvic acid). 2-para-methoXy-phenyl-quinolin-4: 6 dicarboxylic acid 6-ethyl-ester, (from para-anisic- .aldehyde, para-amino-ethyl-benzoate, and

I pyruvic acid) 2-para-oxy-meta-methoxyphenyl-quinolin-lz6-dioarboxylic acid 6- ethyl ester, (from. vanillin, para-aminoethyl-benzoate, and pyruvicjacid). All of these are yellow to white crystalline powders slightly soluble in alcohol, insoluble in water and melting at, high temperatures.

They are soluble with decomposition in alkalies.

strong sulfuric acid and in hot concentrated In general the process is as follows :One molecular proportion of an ester of paraamino-benzoic-acid is dissolved in absolute alcohol on heating. The solution is placed in a flask and connected to a reflux condenser andheated to boiling. .Thereis now added one molecular proportion of aromatic aldehyde diluted with its own volume of absolute alcohol and the resulting mixture boiled ten minutes: One molecular proportion of pyruvic acid is now allowed to run in slowly through the condenser and iii a short timethe condensation product, the new quinolin derivative, begins to crystallize out or Will do so if the mixture be boiled, for an hour Specification of Letters Patent.

Application filed May 20,

QUINOLIN COMPOUNDS AND PROOESS OFHZP RODUCING SAME.

1914. Serial No. 839,842.

Patented May 11', lti l'li.

and then let stand. The com n m g;

purified by recrystallizing from absolute al- The ester produced may be expressedby' the following general formula in which X is any aryl group and Y any monovalent radical. In carrying out the process in detail, takinga particular product, one may proceed as follows :-188'parts by weight ofpara-aminoethylbenzoate are dissolved in 200 parts of hot absolute alcohol and this'solution placed in a flask connected to a reflux condenser, l06p arts of benzaldehyde diluted with 106 parts of absolute alcohol are added and the resulting mixture boiled ten minutes. 88 parts of pyruvic acid are now run in through the, condenser. After boiling a short time the whole mass suddenly solidifies. 500 parts of 90% alcohol are now added and the mass broken by shaking until it is a thick paste. This is poured on to a filter and the liquor removed by suction. The residue on the filter is brokenup and purified by wash ing and recrystallizing from alcohol, the finished product being a white crystalline powder. It is Z-phehyl-quinolin-l:6dicar boxylic acid 6-ethyl ester and has the formula in which X is any aryl group monovalent radical. r

and Y any of quinolin w 2.;An ester of 2-phenyl-quinolin-4:6-dicarboxylic acid. 1-: p '3. 2-phenyl-quinolin 4;; 6 dicarboxylic 6 ethyl ester.

5. .-4,.The-p'rocess of producing, derivatives ti quinolin-which consists in condensing an i .eisterof paraamino-benzoic acid and an'aromane aldehyde with pyruvic acld.

- '5. The process of producing derivatives 10 of flquinolin consisting in boiling together in absolute alcoholic solution,

equimolecular proportions of an ester of para-amino-benfz'biieiacid, anaromatic aldehyde'and pyruvic 15 fgfii-The process producing .a derivative I ui-nolin byboiling together in absolute a a o i f -be'nzaldehyde, pa.a-aInmo-ethyl-benaoate olic solution eo'i'lmolecular proportions pyruvic ac d.

'ch consists in dissolving subs of producing a. derivative paste, removing the liquor and purifying the residue. p p

In witness whereof, I have hereunto set my hand and seal at Indianapolis, Indiana, this sixth day of May, A. D. nineteen hundred and fourteen.

ALEX B. DAVIS. [L. s Witnesses:

E. G. EBERHARDT, I, ARTHUR L. WALTERS. 

